The synthesis of (-)-muricatacin starting from 1-bromododecane and 2-p
entyn-1-ol is described. 2-Pentadecyn-1-ol (4), which was prepared fro
m 1-bromododecane (2) and 2-pentyn-1-ol (3), was converted to epoxy al
cohol 6 through a two-step reaction sequence, 6 being successively sub
mitted to tosylation, iodination, chain extension with tert-butyl lith
ioacetate, and acid-catalyzed cyclization to give (-)-muricatacin (1a)
. Recrystallization afforded optically pure 1a.